o-Methylphenylphenylacetylene 3b
100.0 mg, 52%; oil;
IR (film): 2360, 2335, 1599, 1571, 1493, 1455, 1379, 1157, 1103, 1069, 912, 754, 714, 689, 554, 521, 449 cm–1;
1H NMR (400 MHz, CDCl3, TMS, ppm): δ 7.45 (s, 2H), 7.41 (s, 1H), 7.25 (s, 3H), 7.14 (s, 2H), 7.07 (s, 1H), 2.431 (s, 3H);
13C NMR (100 MHz, CDCl3, ppm): δ 140.2, 131.9, 131.6, 129.5, 128.4 (d), 128.2, 125.6, 123.6, 123.1, 93.4, 88.4, 20.8;
MS (EI, 70 eV):m/z (%) 192(97) [M+], 191 (100) [M+ – 1], 189 (36), 65 (26); known compound (14309-60-5).(12a)
12 a) Kakusawa, N.; Yamaguchi, K.; Kurita, J. J. Organomet. Chem. 2005, 690, 2956– 2966, DOI: 10.1016/j.jorganchem.2005.03.021
Gram-Scale Preparation of Pd@PANI: A Practical Catalyst Reagent for Copper-Free and Ligand-Free Sonogashira Couplings
Jiangsu Co-innovation Center for Prevention and Control of Important Animal Infectious Diseases and Zoonoses, Jiangsu Key Laboratory of Zoonosis, School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002,People’s Republic of China
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00322
Publication Date (Web): November 18, 2016
Copyright © 2016 American Chemical Society
*E-mail: yulei@yzu.edu.cn.
Abstract
Palladium nanoparticles on the polyaniline (Pd@PANI) catalyst are now easily prepared on a gram scale through the oxidative polymerization of aniline in the presence of PdCl2 by using air as a clean oxidant. The material is found to be very stable and can be stored for more than one year without deactivation. Thus, it may become a commercial reagent in organic synthesis, depending on its application scopes. This article reported the first example of Pd@PANI-catalyzed Sonogashira couplings free of copper and ligands.
